3-methyl-2-phenyl-1,2,3,4-tetrahydroquinoline | 24005-26-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3-methyl-2-phenyl-1,2,3,4-tetrahydroquinoline
• CAS: 24005-26-3
• 化学式: C₁₆H₁₇N
• 分子量: 223.318
• InChiKey: LNYOPJXSBMZLKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-苯基-3-甲基-喹啉 在 磷酸二苯酯 、 二氢吡啶 作用下， 以 苯 为溶剂， 反应 12.0h， 以86%的产率得到3-methyl-2-phenyl-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  无金属布朗斯台德酸催化转移氢化 - 喹啉的新型有机催化还原

  摘要：

  已经开发出第一个使用 Hantzsch 二氢吡啶作为氢源的无金属布朗斯台德酸催化喹啉加氢。这种迄今为止前所未有的杂芳族化合物的有机催化还原提供了多种不同取代的 1,2,3,4-四氢喹啉，在温和的反应条件下，使用非常少量的布朗斯台德酸催化剂，产率极好。

  DOI：

  10.1055/s-2006-939706

文献信息

• Synthesis of Tetrahydroquinolines via Borrowing Hydrogen Methodology Using a Manganese PN³ Pincer Catalyst
  作者：Natalie Hofmann、Leonard Homberg、Kai C. Hultzsch

  DOI：10.1021/acs.orglett.0c02905

  日期：2020.10.16

  simple secondary alcohols is reported. This one-pot cascade reaction is based on the borrowing hydrogen methodology promoted by a manganese(I) PN3 pincer complex. The reaction selectively leads to 1,2,3,4-tetrahydroquinolines thanks to a targeted choice of base. This strategy provides an atom-efficient pathway with water as the only byproduct. In addition, no further reducing agents are required.

  据报道，从2-氨基苄醇和简单的仲醇开始，直接，选择性地合成1,2,3,4-四氢喹啉。此一锅式级联反应基于锰（I）PN 3钳状络合物促进的借用氢方法。由于有选择地选择了碱，该反应选择性地产生了1,2,3,4-四氢喹啉。该策略提供了以水为唯一副产物的原子有效途径。另外，不需要其他的还​​原剂。
• Simple silver(<scp>i</scp>)-salt catalyzed selective hydroboration of isocyanates, pyridines, and quinolines
  作者：Vipin K. Pandey、Sangita Sahoo、Arnab Rit

  DOI：10.1039/d2cc00491g

  日期：——

  AgSbF6 has been established as an effective catalyst for the hydroboration of structurally and electronically diverse isocyanates under ligand- and solvent-free conditions which selectively yielded either N-boryl formamides or N-boryl methylamines under different conditions. Further, various N-heterocycles can be selectively hydroborated using this simple catalytic system; pyridine derivatives undergo

  AgSbF 6已被确定为在无配体和无溶剂条件下对结构和电子不同的异氰酸酯进行硼氢化的有效催化剂，在不同条件下选择性地产生 N-硼基甲酰胺或 N-硼基甲胺。此外，使用这种简单的催化系统可以选择性地对各种 N-杂环进行硼氢化；吡啶衍生物优先进行 1,4 硼氢化，而对于喹啉，观察到通过完全杂环氢化形成四氢喹啉（水解后） 。
• Selective Catalytic Hydrogenation of Heteroarenes with <i>N</i>-Graphene-Modified Cobalt Nanoparticles (Co₃O₄–Co/NGr@α-Al₂O₃)
  作者：Feng Chen、Annette-Enrica Surkus、Lin He、Marga-Martina Pohl、Jörg Radnik、Christoph Topf、Kathrin Junge、Matthias Beller

  DOI：10.1021/jacs.5b06496

  日期：2015.9.16

  Cobalt oxide/cobalt-based nanopartides featuring a core shell structure and nitrogen-doped graphene layers on alumina are obtained by pyrolysis of Co(OAc)(2)/phenanthroline. The resulting core shell material (Co3O4 Co/NGr@alpha-Al2O3) was successfully applied in the catalytic hydrogenation of a variety of N-heteroarenes including quinolines, acridines, benzo[h], and 1,5-naphthyridine as well as unprotected indoles. The peculiar structure of the novel heterogeneous catalyst enables activation of molecular hydrogen at comparably low temperature. Both high activity and selectivity were achieved in these hydrogenation processes, to give important building blocks for bioactive compounds as well as the pharmaceutical industry.
• GOGTE V. N.; MUKHEDKAR V. A.; M-EL NAMAKY H.; SALAMA M. A.; TILAK B. D., INDIAN J. CHEM. <IJOC-AP>, 1974, 12, NO 12, 1234-1237
  作者：GOGTE V. N.、 MUKHEDKAR V. A.、 M-EL NAMAKY H.、 SALAMA M. A.、 TILAK B. D.

  DOI：——

  日期：——
• Metal-Free Brønsted Acid Catalyzed Transfer Hydrogenation - New Organocatalytic Reduction of Quinolines
  作者：Magnus Rueping、Thomas Theissmann、Andrey Antonchick

  DOI：10.1055/s-2006-939706

  日期：——

  metal-free Bronsted acid catalyzed hydrogenation of quinolines using Hantzsch dihydropyridine as the hydrogen source has been developed. This, so far unprecedented organocatalytic reduction of heteroaromatic compounds provides a variety of differently substituted 1,2,3,4-tetrahydroquinolines in excellent yields under mild reaction conditions using a remarkably low amount of Bronsted acid catalyst.

  已经开发出第一个使用 Hantzsch 二氢吡啶作为氢源的无金属布朗斯台德酸催化喹啉加氢。这种迄今为止前所未有的杂芳族化合物的有机催化还原提供了多种不同取代的 1,2,3,4-四氢喹啉，在温和的反应条件下，使用非常少量的布朗斯台德酸催化剂，产率极好。